Sodium Azide → HCID 57241986, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (2S,4S)-1-p-methoxybenzyloxycarbonyl-4-tritylthiopyrrolidine-2-methanol methanesulfonate (27.81 g) in dimethylformamide (120 ml), a solution (12 ml) of sodium azide (3.50 g: 53.8 mmole) in water is added. The mixture is stirred at 80° C. for 8 hours. The reaction mixture is poured into ice water and extracted with ethyl acetate. The extract is successively washed with water and brine and concentrated. The residue is purified by silica gel column chromatography to give (2S,4S)-1-p-methoxybenzyloxycarbonyl-2-azidomethyl-4-tritylthiopyrrolidine (17.27 g: 30.64 mmole). Total yield of Steps 4 and 5: 74%. NMR δ(CDCl3) ppm: 3.84(s, 3H), 4.82 to 5.15(m, 2H). IR ν (CHCl3) cm-1 : 2105, 1685.

Provenance & Evidence